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416916

Sigma-Aldrich

Dicyclohexyliodoborane

97%

Synonym(s):

Dicyclohexylboryl iodide

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About This Item

Linear Formula:
(C6H11)2BI
CAS Number:
55382-85-9
Molecular Weight:
304.02
MDL number:
MFCD00192014
UNSPSC Code:
12352101
PubChem Substance ID:
24866084
NACRES:
NA.22

Assay

97%

form

liquid

reaction suitability

reagent type: reductant

bp

198-200 °C/1.25 mmHg (lit.)

density

1.325 g/mL at 25 °C (lit.)

SMILES string

IB(C1CCCCC1)C2CCCCC2

InChI

1S/C12H22BI/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2

InChI key

RWFGGTOYIFQXAO-UHFFFAOYSA-N

Application

Dicyclohexyliodoborane (Chx2BI) can be used as a reagent:
  • For the enolboration of esters and tertiary amides to synthesize corresponding Z or E enolates.[1][2]
  • In the stereoselective preparation of β-hydroxy-α-trifluoromethyl carboxylic acids via haloborane-mediated diastereoselective aldol addition of aldehydes with trifluoropropanoic acid.[3]
  • In the total synthesis of pordamacrine A,[4] and trocheliophorolide D.[5]

Reactant for:
  • Preparation of vinyloxyboranes

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

86.0 °F - closed cup

Flash Point(C)

30 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM9013
SHBD6679V
SHBD5388V
SHBD7436V
43296EM

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Diastereoselective synthesis of anti-3-hydroxy-2-trifluoromethyl carboxylic acids
Ramachandran PV, et al.
Tetrahedron Letters, 56(23), 3019-3022 (2015)
Total Synthesis of the Proposed Structure of Trocheliophorolide D
Hwang S, et al.
European Journal of Organic Chemistry, 2011(36), 7414-7418 (2011)
A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A
Seizert, Curtis A and Ferreira, Eric M
Tetrahedron, 73(29), 4186-4194 (2017)
Enolboration. 6. Dicyclohexyliodoborane, a Versatile Reagent for the Stereoselective Synthesis of Either Z or E Enolates from Representative Esters
Ganesan K and Brown HC
The Journal of Organic Chemistry, 59(9), 2336-2340 (1994)
Dicyclohexyliodoborane/Triethylamine-a new reagent which achieves the facile enolboration of esters and tertiary amides
Brown HC and Ganesan K
Tetrahedron Letters, 33(24), 3421-3424 (1992)

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